铜促进的三氟甲基化反应研究进展
收稿日期: 2013-11-09
修回日期: 2013-12-23
网络出版日期: 2014-01-02
基金资助
国家自然科学基金（Nos. 21272050，21072040）资助项目.
Recent Advances in Copper-Promoted Trifluoromethylation Reactions
Received date: 2013-11-09
Revised date: 2013-12-23
Online published: 2014-01-02
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21272050, 21072040).
王光祖 , 赫侠平 , 戴建军 , 许华建 . 铜促进的三氟甲基化反应研究进展[J]. 有机化学, 2014 , 34(5) : 837 -851 . DOI: 10.6023/cjoc201311012
Drug molecules that contain trifluoromethyl group can effectively improve their lipophilicity, absorbability and metabolic stability. Thus, considerable attention has been paid to the introduce of trifluoromethyl group into organic molecules. Recently, transition metal-catalyzed trifluoromethylation has been well developed. The cheap and high activity copper catalyst has also been used to access a variety of trifluoromethylation reactions. In this review, we focus the conversion of a number of substrates including halogenated hydrocarbons, boron reagents, C—H compounds, amines and carboxylic acids into the corresponding trifluoromethyl-containing compounds.
Key words： copper-catalyzed; trifluoromethylation; trifluoromethyl reagents
[1] (a) Uneyama, K. Organofluorine Chemistry, Blackwell, Oxford, U. K., 2006.
(b) Hird, M. Chem. Soc. Rev. 2007, 36, 2070.
(c) Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305.
(d) O'Hagan, D. Chem. Soc. Rev. 2008, 37, 308.
(e) Ojima, I. Fluorine in Medicinal Chemistry and Chemical Biology, Wiley-Blackwell, Chichester, U.K., 2009.
(f) Filler, R.; Saha, R. Future Med. Chem. 2009, 1, 777.
(g) Daniels, S.; Tohid, S. F. M.; Velanguparackel, W.; Westwell, A. D. Expert Opin. Drug Discovery 2010, 5, 291.
(h) Acena, J. L.; Simon-Fuentes, A.; Fustero, S. Curr. Org. Chem. 2010, 14, 928.
(i) Wang, X.; Zhang, Y.; Wang, J. Sci. Sin. Chim. 2012, 42, 1417.
(j) Yu, H. Z; Su. S. Q, Zhang , C; Dang, Z. M. Chin. J. Org. Chem. 2013, 33, 1628 (in Chinese).
(于海珠, 苏圣钦, 张弛, 党智敏, 有机化学, 2013, 33, 1628.)
(k) Liu, T. F; Shen, Q, L. Eur. J. Org. Chem.2012, 6679.
[2] (a) Welch, J. T. Tetrahedron 1987, 43, 3123.
(b) Kirsch, P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications, Wiley-VCH, Weinheim, 2004.
(c) Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2005, 44, 214. (d) Schlosser, M. Angew. Chem., Int. Ed. 2006, 45, 5432.
(e) Muller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
(f) Bonnet-Delpon, D. Bioorganic and Medicinal Chemistry of Fluorine, Wiley-VCH, Hoboken, NJ, 2008.
(g) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
(h) Hagmann, W. K. J. Med. Chem. 2008, 51, 4359.
(i) Pursor, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
(j) Ojima, I. Fluorine in Medicinal Chemistry and Chemical Biology, Wiley-Blackwell, Chichester, 2009.
(k) Lin, G.-Q.; You, Q.-D.; Cheng, J.-F. Chiral Drugs: Chemistry and Biological Action, Wiley-VCH, Hoboken, 2011.
[3] (a) Swarts, F. Bull. Acad. R. Belg. 1892, 24, 309.
(b) Boswell, G. A., Jr.; Ripka, W. C.; Scribner, R. M.; Tullock, C. W. Org. React. 1974, 21, 1.
[4] Kazuyuki, S.; Masaaki, O.; Akira, A.; Itsumaro, K. Org. Lett. 2013, 23, 4359.
[5] (a) Mizuta, S.; Verhoog, S.; Engle, K. M.; Khotavivattana, T.; O'Duill, M.; Wheelhouse, K.; Rassias, G.; Medebielle, M.; Gouverneur, V. J. Am. Chem. Soc. 2013, 135, 2505.
(b) Yasu, Y.; Koike, T.; Akita, M. Org. Lett. 2013, 15, 2137.
(c) Herrmann, A. T.; Smith, L. L.; Zakarian, A. J. Am. Chem. Soc. 2012, 134, 6976.
(d) Iqbal, N.; Choi, S.; Kim, E.; Cho, E. J. J. Org. Chem. 2012, 77, 11383.
(e) Mizuta, S.; Engle, K. M.; Verhoog, S.; Galicia-López, O.; O'Duill, M.; Médebielle, M.; Wheelhouse, K.; Rassias, G.; Thompson, A. L.; Gouverneur, V. Org. Lett. 2013, 15, 1250.
[6] (a) Wang, X.; Truesdale, L.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3648.
(b) Ye, Y.; Ball, N. D.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2010, 132, 14682.
(c) Ball, N. D.; Gary, J. B.; Ye, Y.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 7577.
(d) Cho, E. J.; Buchwald, S. L. Org. Lett. 2011, 13, 6552.
(e) Hafner, A.; Brase, S. Angew. Chem., Int. Ed. 2012, 51, 3713.
(f) Zhang, X. G.; Dai, H. X.; Wasa, M.; Yu, J. Q. J. Am. Chem. Soc. 2012, 134, 11948.
[7] (a) Hafner, A.; Bihlmeier, A.; Nieger, M.; Klopper, W.; Brase, S. J. Org. Chem. 2013, 78, 7938.
(b) Hafner, A.; Feuerstein, T. J.; Bräse, S. Org. Lett. 2013, 15, 3468.
(c) Ye, Y.; Lee, S. H.; Sanford, M. S. Org. Lett. 2011, 13, 5464.
(d) Wang, X.; Xu, Y.; Mo, F.; Ji, G.; Qiu, D.; Feng, J.; Ye, Y.; Zhang, S.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2013, 135, 10330.
(e) Zeng, Y.; Zhang, L.; Zhao, Y.; Ni, C.; Zhao, J.; Hu, J. J. Am. Chem. Soc. 2013, 135, 2955.
[8] (a) Dubinina, G. G.; Brennessel, W. W.; Miller, J. L.; Vicic, D. A. Organometallics 2008, 27, 3933.
(b) Hao, F.; Jiang, H. W.; Zong, G.; Zhou, Z.; Du, R. B.; Chen, Q. Y.; Xiao, J. C. J. Org. Chem. 2012, 77, 3604.
(c) Gao, J. R.; Wu, H.; Xiang, B.; Yu, W. B.; Han, L.; Jia, Y. X. J. Am. Chem. Soc. 2013, 135, 2983.
[9] (a) Parsons, A. T.; Senecal, T. D.; Buchwald, S. L. Angew. Chem., Int. Ed. 2012, 51, 2947.
(b) Patra, T.; Deb, A.; Manna, S.; Sharma, U.; Maiti, D. Eur. J. Org. Chem. 2013, 2013, 5247.
[10] (a) Kobayashi, Y.; Kumadaki, I. Tetrahedron Lett. 1969, 10, 4095. (b) Kobayashi, Y.; Yamamoto, K.; Kumadaki, I. Tetrahedron Lett. 1979, 20, 4071.
[11] (a) Kondratenko, N. V.; Vechirko, E. P.; Yagupolskii, L. M. Synthesis 1980, 932.
(b) Kremlev, M. M.; Tyrra, W.; Mushta, A. I.; Naumann, D.; Yagupolskii, Y. L. J. Fluorine Chem. 2010, 131, 212.
(c) Nowak, I. Robins, M. J. J. Org. Chem. 2007, 72, 2678.
[12] (a) Burton, D. J.; Wiemers, D. M. J. Am. Chem. Soc. 1985, 107, 5014.
(b) Burton, D. J.; Wiemers, D. M. J. Am. Chem. Soc. 1986, 108, 832.
(c) Clark, J. H.; McClinton, M. A.; Blade, R. J. J. Chem. Soc., Chem. Commun. 1988, 638.
[13] Carr, G. E.; Chambers, R. D.; Holmes, T. F.; Parker, D. G. J. Chem. Soc., Perkin Trans. 1 1988, 921
[14] Su, D. B.; Duan, J. X.; Chen, Q. Y. Tetrahedron Lett. 1991, 32, 7689.
[15] Chen, Q. Y.; Duan, J. X. J. Chem. Soc., Chem. Commun. 1993, 1389.
[16] (a) McLoughlin, V. C. R.; Thrower, J. Tetrahedron 1969, 25, 5921.
(b) Lin, T. S.; Gao, Y. S. J. Med. Chem. 1983, 26, 598.
(c) Duan, J. X.; Su, D. B.; Wu, J. P.; Chen, Q. Y. J. Fluorine Chem. 1994, 66, 167.
(d) Su, D. B.; Duan, J. X.; Chen, Q. Y. Tetrahedron Lett. 1991, 32, 7689.
(e) Su, D. B.; Duan, J. X.; Yu, A.; Chen, Q. Y. J. Fluorine Chem. 1993, 65, 11.
(f) Langlois, B. R.; Roques, N. J. Fluorine Chem. 2007, 128, 1318.
(g) Qing, F. Chin. J. Org. Chem. 2012, 32, 815 (in Chinese).
(卿凤翎, 有机化学, 2012, 32, 815.)
[17] (a) Yang, C.-T.; Zhang, Z.-Q.; Liu, Y.-C.; Liu, L. Angew. Chem., Int. Ed. 2011, 50, 3904.
(b) Yang, C.-T.; Zhang, Z.-Q.; Liang, J.; Liu, J.-H.; Lu, X.-Y.; Chen, H.-H.; Liu, L. J. Am. Chem. Soc. 2012, 134, 11124.
(c) Yang, C.-T.; Zhang, Z.-Q.; Tajuddin, H.; Wu, C.-C.; Liang, J.; Liu, J.-H.; Fu, Y.; Czyzewska, M.; Steel, P. G.; Marder, T. B.; Liu, L. Angew. Chem., Int. Ed. 2012, 51, 528.
(d) Ren, P.; Stern, L.-A.; Hu, X. Angew. Chem., Int. Ed. 2012, 51, 9110.
(e) Nishino, M.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2012, 51, 6993.
(f) Wu, J.-C.; Song, R.-J.; Wang, Z.-Q.; Huang, X.-C.; Xie, Y.-X.; Li, J.-H. Angew. Chem., Int. Ed. 2012, 51, 6993.
(g) Kitching, M. O.; Hurst, T. E.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51, 2925.
(h) Wang, L.; Huang, H.; Priebbenow, D. L.; Pan, F.-F.; Bolm, C. Angew. Chem., Int. Ed. 2013, 52, 3478.
(i) Uyeda, C.; Tan, Y.; Fu, G. C.; Peters, J. C. J. Am. Chem. Soc. 2013, 135, 9548.
(j) Deng, W.; Liu, L.; Guo, Q.-X. Chin. J. Org. Chem. 2004, 24, 150 (in Chinese).
(邓维, 刘磊, 郭庆祥, 有机化学, 2004, 24, 150.)
(k) Xu, H.-J.; Man, Q.-S.; Lin, Y.-C.; Li, Y.-Y.; Feng, Y.-S. Chin. J. Org. Chem. 2010, 30, 9 (in Chinese).
(许华建, 蔄秋石, 林义成, 李源源, 冯乙巳, 有机化学, 2010, 30, 9.)
[18] Dubinina, G. G.; Furutachi, H.; Vicic, D. A. J. Am. Chem. Soc. 2008, 130, 8600.
[19] Oishi, M.; Kondo, H.; Amii, H. Chem. Commun. 2009, 1909.
[20] Zhang, S.-L.; Liu, L.; Fu, Y.; Guo, Q.-X. Organometallics 2007, 26, 4546.
[21] Morimoto, H.; Tsubogo, T.; Litvinas, N. D.; Hartwig, J. F. Angew. Chem., Int. Ed. 2011, 50, 3793.
[22] (a) Zanardi, A.; Novikov, M. A.; Martin, E.; Benet-Buchholz, J.; Grushin, V. V. J. Am. Chem. Soc. 2011, 133, 20901.
(b) Tomashenko, O. A.; Escudero-Adan, E. C.; Belmonte, M. M.; Grushin, V. V. Angew. Chem., Int. Ed. 2011, 50, 7655.
[23] Zhang, C. P.; Wang, Z. L.; Chen, Q. Y.; Zhang, C. T.; Gu, Y. C.; Xiao, J. C. Angew. Chem., Int. Ed. 2011, 50, 1896.
[24] Weng, Z.; Lee, R.; Jia, W.; Yuan, Y.; Wang, W.; Feng, X.; Huang, K. W. Organometallics 2011, 30, 3229.
[25] Kondo, H.; Oishi, M.; Fujikawa, K.; Amii, H. Adv. Synth. Catal. 2011, 353, 1247.
[26] Knauber, T.; Arikan, F.; Roschenthaler, G.-V.; Goossen, L. J. Chem. Eur. J. 2011, 17, 2689.
[27] Schareina, T.; Wu, X.-F.; Zapf, A.; Cotté, A.; Gotta, M.; Beller, M. Top. Catal. 2012, 55, 426.
[28] Duan, C.; Li, Y.; Chen, T.; Wang, H.; Zhang, R.; Jin, K.; Wang, X. Synlett 2011, 1713.
[29] Chen, M.; Buchwald, S. L. Angew. Chem., Int. Ed. 2013, 52, 11628.
[30] Hafner, A.; Braese, S. Adv. Synth. Catal. 2011, 353, 3044.
[31] Kawai, H.; Furukawa, T.; Nomura, Y.; Tokunaga, E.; Shibata, N. Org. Lett. 2011, 13, 3596.
[32] Miyake, Y.; Ota, S.; Nishibayashi, Y. Chem.-Eur. J. 2012, 18, 13255.
[33] Miyake, Y.; Ota, S.; Shibata, M.; Nakajima, K.; Nishibayashi, Y. Chem. Commum. 2013, 49, 7809.
[34] Larsson, J. M.; Pathipati, S. R.; Szabo, K. J. J. Org. Chem. 2013, 78, 7330.
[35] Zhao, T. S.; Szabo, K. J. Org. Lett. 2012, 14, 3966.
[36] Novak, P.; Lishchynskyi, A.; Grushin, V. V. J. Am. Chem. Soc. 2012, 134, 16167.
[37] Ambler, B. R.; Altman, R. A. Org. Lett. 2013.
[38] Chu, L.; Qing, F.-L. Org. Lett. 2010, 12, 5060.
[39] Senecal, T. D.; Parsons, A. T.; Buchwald, S. L. J. Org. Chem. 2011, 76, 1174.
[40] Xu, J.; Luo, D. F.; Xiao, B.; Liu, Z. J.; Gong, T. J.; Fu, Y.; Liu, L. Chem. Commun. 2011, 47, 4300.
[41] Zhang, C. P.; Cai, J.; Zhou, C. B.; Wang, X. P.; Zheng, X.; Gu, Y. C.; Xiao, J. C. Chem. Commun. 2011, 47, 9516.
[42] Liu, T.; Shen, Q. Org. Lett. 2011, 13, 2342.
[43] Huang, Y.; Fang, X.; Lin, X.; Li, H.; He, W.; Huang, K.-W.; Yuan, Y.; Weng, Z. Tetrahedron 2012, 68, 9949.
[44] Ji, Y.; Brueckl, T.; Baxter, R. D.; Fujiwara, Y.; Seiple, I. B.; Su, S.; Blackmond, D. G.; Baran, P. S. Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 14411.
[45] Ye, Y.; Kunzi, S. A.; Sanford, M. S. Org. Lett. 2012, 14, 4979.
[46] Li, Y.; Wu, L.; Neumann, H.; Beller, M. Chem. Commun. 2013, 49, 2628.
[47] Litvinas, N. D.; Fier, P. S.; Hartwig, J. F. Angew. Chem., Int. Ed. 2012, 51, 536.
[48] Liu, T.; Shao, X.; Wu, Y.; Shen, Q. Angew. Chem., Int. Ed. 2012, 51, 555.
[49] Novák, P.; Lishchynskyi, A.; Grushin, V. V. Angew. Chem., Int. Ed. 2012, 51, 7767.
[50] Khan, B. A.; Buba, A. E.; Goossen, L. J. Chem.-Eur. J. 2012, 18, 1577.
[51] Ye, Y.; Sanford, M. S. J. Am. Chem. Soc. 2012, 134, 9034.
[52] Xu, J.; Xiao, B.; Xie, C. Q.; Luo, D. F.; Liu, L.; Fu, Y. Angew. Chem., Int. Ed. 2012, 51, 12551.
[53] Zheng, H.; Huang, Y.; Wang, Z.; Li, H.; Huang, K.-W.; Yuan, Y.; Weng, Z. Tetrahedron Lett. 2012, 53, 6646.
[54] Chu, L.; Qing, F.-L. J. Am. Chem. Soc. 2010, 132, 7262.
[55] Weng, Z.; Li, H.; He, W.; Yao, L.-F.; Tan, J.; Chen, J.; Yuan, Y.; Huang, K.-W. Tetrahedron 2012, 68, 2527.
[56] Luo, D.-F.; Xu, J.; Fu, Y.; Guo, Q.-X. Tetrahedron Lett. 2012, 53, 2769.
[57] Zhang, K.; Qiu, X.-L.; Huang, Y.; Qing, F.-L. Eur. J. Org. Chem. 2012, 58.
[58] Shimizu, R.; Egami, H.; Nagi, T.; Chae, J.; Hamashima, Y.; Sodeoka, M. Tetrahedron Lett. 2010, 51, 5947.
[59] Chu, L.; Qing, F. L. J. Am. Chem. Soc. 2012, 134, 1298.
[60] Pair, E.; Monteiro, N.; Bouyssi, D.; Baudoin, O. Angew. Chem., Int. Ed. 2013, 52, 5346.
[61] Feng, C.; Loh, T.-P. Chem. Sci. 2012, 3, 3458.
[62] Ilchenko, N. O.; Janson, P. G.; Szabo, K. J. Chem. Commun. 2013, 49, 6614.
[63] Wang, X.; Ye, Y.; Ji, G.; Xu, Y.; Zhang, S.; Feng, J.; Zhang, Y.; Wang, J. Org. Lett. 2013, 15, 3730.
[64] Xu, J.; Fu, Y.; Luo, D. F.; Jiang, Y. Y.; Xiao, B.; Liu, Z. J.; Gong, T. J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 15300.
[65] Parsons, A. T.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 9120.
[66] Wang, X.; Ye, Y.; Zhang, S.; Feng, J.; Xu, Y.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2011, 133, 16410.
[67] Chu, L.; Qing, F.-L. Org. Lett. 2010, 14, 2106.
[68] Mitsudera, H.; Li, C.-J. Tetrahedron Lett. 2011, 52, 1898.
[69] (a) Chu, L. L.; Qing, F. L. Chem. Commun. 2010, 46, 6285.
(b) Xiao, H. Q.; Huang, Y. Z.; Qing, F.-L. Tetrahedron 2010, 21, 2949.
[70] Hu, M.; Ni, C.; Hu, J. J. Am. Chem. Soc. 2012, 134, 15257.
[71] Dai, J. J.; Fang, C.; Xiao, B.; Yi, J.; Xu, J.; Liu, Z. J.; Lu, X.; Liu, L.; Fu, Y. J. Am. Chem. Soc. 2013, 135, 8436.
[72] Danoun, G.; Bayarmagnai, B.; Grunberg, M. F.; Goossen, L. J. Angew. Chem., Int. Ed. 2013, 52, 7972.
[73] (a) Shang, R.; Liu, L. Sci. China Chem. 2011, 54, 1670.
(b) Shang, R.; Fu, Y.; Li, J.-B.; Zhang, S.-L.; Guo, Q.-X.; Liu, L. J. Am. Chem. Soc. 2009, 131, 5738.
(c) Shang, R.; Yang, Z. W.; Wang, Y.; Zhang, S.-L.; Liu, L. J. Am. Chem. Soc. 2010, 132, 14391.
(d) Dai, J.-J.; Liu, J.-H.; Luo, D.-F.; Liu, L. Chem. Commun. 2011, 47, 677.
[74] Li, Z. J; Cui, Z. L; Liu Z. Q. Org. Lett. 2013, 15, 406.
[75] He, Z.; Luo, T.; Hu, M.; Cao, Y.; Hu, J. Angew. Chem., Int. Ed. 2012, 51, 3944.
[76] He, Z.; Zhang, R.; Hu, M.; Li, L.; Ni, C.; Hu, J. Chem. Sci. 2012, 4, 3478.
[77] Anna E. A. ; David W. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2012, 132, 4986.
[78] (a) Nagib, D. A.; Scott, M. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 10875.
(b) Nagib, D. A.; MacMillan, D. W. C. Nature 2011, 480, 224.
(c) Pham, P. V.; Nagib, D. A.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2011, 50, 6119.
(d) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
[79] Deng, Q. H.; Wadepohl, H.; Gade, L. H. J. Am. Chem. Soc. 2012, 134, 10769.
[80] Janson, P. G.; Ghoneim, I.; Ilchenko, N. O.; Szabó, K. J. Org. Lett. 2012, 14, 2882.
[81] Zhu, R.; Buchwald, S. L. J. Am. Chem. Soc. 2012, 134, 12462.
[82] Ilchenko, N. O.; Janson, P. G.; Szabo, K. J. J. Org. Chem. 2013, 78, 11087.
[83] Kong, W.; Casimiro, M.; Merino, E.; Nevado, C. J. Am. Chem. Soc. 2013, 135, 14480.
[84] Egami, H.; Shimizu, R.; Sodeoka, M. J. Fluorine Chem. 2013, 152, 51.
[85] Zhang, Y. Q.; Liu, J. D.; Xu, H. Org. Biomol. Chem. 2013, 11, 6242.
[86] Liu, X.; Xiong, F.; Huang, X.; Xu, L.; Li, P.; Wu, X. Angew. Chem., Int. Ed. 2013, 52, 6962.
[87] Chen, Z. M.; Bai, W.; Wang, S. H.; Yang, B. M.; Tu, Y. Q.; Zhang, F. M. Angew. Chem., Int. Ed. 2013, 52, 9781.
[88] Qing, F.-L.; Chu, L. Synthesis 2012, 44, 1521.Lin, X.; Wang, G.; Li, H.; Huang, Y.; He, W.; Ye, D.; Huang, K.-W.; Yuan, Y.; Weng, Z. Tetrahedron 2013, 69, 2628.
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